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Compound i and compound ii and their preparation methods and applications

A compound and reaction technology, applied in the field of compound I and compound II and their preparation, can solve problems such as poor therapeutic effect and adverse reactions, and achieve the effect of slowing down growth

Active Publication Date: 2017-04-19
SHENZHEN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to provide structural formula as the compound of formula I and formula II and its preparation method and application, i.e. compound I and compound II and its preparation method and application, specifically provide T7 (the first reactant) and EA (the second Two reactant) the compound of the brand-new formula I of the structure that obtains by coupling, and by the compound of formula I joint ROR1 (the 3rd reactant) covalently obtains the compound of brand-new formula II, solves EA and ROR1 in the prior art Poor therapeutic effect and adverse reactions caused by inability to induce immune response

Method used

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  • Compound i and compound ii and their preparation methods and applications
  • Compound i and compound ii and their preparation methods and applications
  • Compound i and compound ii and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0048] Weigh 344mg (1mmol) T7 and 341mg (1.125mmol) EA and dissolve in 8mL DMF, add HBTU (427mg, 1.125mmol), triethylamine (416μL, 3mmol) and a catalytic amount of DMAP, and stir the reaction at room temperature for 12 hours. The reaction solution was poured into 100 mL of water, filtered with suction, and the filter residue was washed with water and dried to obtain a crude product. After separation by column chromatography (DCM:MeOH=20:1), 475 mg of T7-EA was obtained as a white solid with a yield of 75.5%. Purity: 95.08%, ESI-MS: m / z=629.1[M+H] + .(Such as Figure 1-2 shown)

preparation Embodiment 2

[0050] Weigh 172mg (0.5mmol) of T7 and 189.4mg (0.625mmol) of EA and dissolve in 6mL of a mixed solvent of benzene and toluene with a volume ratio of 2:1, add HBTU (237.2mg, 0.625mmol), triethylamine (312μL , 2.25mmol) and a catalytic amount of DMAP, stirred at room temperature for 24 hours. The reaction solution was poured into 100 mL of water, filtered with suction, and the filter residue was washed with water and dried to obtain a crude product. After separation by column chromatography (DCM:MeOH=20:1), 236.8 mg of T7-EA was obtained as a white solid, with a yield of 73.2%.

preparation Embodiment 3

[0052] Weigh 516mg (1.5mmol) of T7 and 568.3mg (1.875mmol) of EA and dissolve in 15mL of tetrahydrofuran, add HBTU (711.7mg, 1.875mmol), triethylamine (520μL, 3.75mmol) and a catalytic amount of DMAP, and stir at room temperature React for 18 hours. The reaction solution was poured into 200 mL of water, filtered with suction, and the filter residue was washed with water and dried to obtain a crude product. After separation by column chromatography (DCM:MeOH=20:1), 752 mg of T7-EA was obtained as a white solid, with a yield of 77.5%.

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Abstract

The present invention relates to compound I and compound II and their preparation methods and applications, wherein the newly synthesized compound of formula I can stimulate anti-tumor innate immunity and cellular immunity in greatly improving the anti-tumor effect of diuretic acid (EA). The drug design of synergistic integration of anti-tumor immunity; proved the immune response mechanism of the compound of formula I against melanoma; the compound of formula II covalently prepared by the compound of formula I and ROR1 significantly slowed down the growth rate of breast cancer subcutaneous xenografts growth, proving the immune response mechanism of the compound of formula II in treating breast cancer, and at the same time proving that the compound of formula I not only has the function of stimulating innate immunity and adaptive immunity, but also has the function of immune adjuvant.

Description

technical field [0001] The present invention relates to the technical field of tumor cancer disease prevention and treatment, and more specifically, relates to compound I and compound II and their preparation methods and applications. Background technique [0002] Malignant melanoma is a highly malignant tumor derived from melanocytes. It is a common malignant tumor in skin cancer and has strong metastases. At present, the main treatment methods are radiotherapy, chemotherapy and surgery. However, traditional treatments cannot completely cure it , with the development of tumor immunology and molecular biology, immunotherapy for tumors has become a research hotspot. Toll like receptors (TLRs) are an important class of pattern recognition receptors, which belong to type I transmembrane proteins and are expressed on various immune cells. TLRs stimulate innate immunity and adaptive immune responses. Play an important role. Agonists of TLRs act on antigen-presenting cells, such...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/18A61P35/00C07K14/705C07K1/107
CPCC07D473/18C07K14/70567C07K19/00A61P35/00C07D487/04A61K31/519C07K1/107C07K14/70503
Inventor 靳广毅王竹林胡云龙刘兵
Owner SHENZHEN UNIV
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